Water → 3-Amino-2,6-di-tert-butylphenol

HRID 2404903Notes

Reaction equation

HRID 2404903 reaction equation
[BH4-].[Na+].[C:3]([C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[C:9]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]=1[OH:20])([CH3:6])([CH3:5])[CH3:4].O>CO.Cl[Ni]Cl>[NH2:13][C:12]1[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])=[C:8]([OH:20])[C:9]([C:16]([CH3:17])([CH3:18])[CH3:19])=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 53962653HCID 53962653, compound

Product 1

HCID 513581793-Amino-2,6-di-tert-butylphenolYield 78%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

NaBH4 (433 mg, 11.45 mmol) was added to a solution of 2,6-di-tert-butyl-3-nitrophenol (950 mg, 3.780 mmol) and NiCl2 (1.24 g, 9.568 mmol) in methanol (15 mL) at −15° C. After the addition was complete, the reaction mixture was stirred for 20 seconds and water was added immediately and the reaction mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and evaporated in vacuo to afford 3-amino-2,6-di-tert-butyl-phenol (650 mg, 78%). 1H NMR (300 MHz, CDCl3) δ 6.92 (d, J=8.4 Hz, 1H), 6.24 (d, J=8.4 Hz, 1H), 5.39 (s, 1H), 1.62 (s, 9H), 1.39 (s, 9H); MS (ESI) m/z: 222.2 [M+H+].

Workup

  1. additionAfter the addition
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-7900385e5f34469da30fa103ba19e7f8
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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